Mordant azo dyestuffs and process of preparing them



Patented Sept. l8, in

- UNITED s Ar-Es PATENT OFFICE.

ALFRED PHILIPS, or FRANKFORT-ON-THE-MAIN, A D MARTIN DABELOW; On'nocnsr-ON-THE-MADL GERMANY, ASSIGNORS 'ro GRASSELLI mmsrurr CORPORATION, on NEWYORK, N. Y., A CORPORATION OF DELAWARE.

J mon'nn'Nr .AZO DYESTUFFS 1ND rRoc ss OF PREPARING. THEM.

No Drawing. Application flledApril 19, 1927, Serial No. 185,065, and inGermany April 27, 1926.

Our present invention relates to mordant azo dyestuffs and a process ofpreparing them. a p p We have found that valuable dyestuffs are 5obtained by combining the 2.6-dihydroxynaphthalehe-ii-carbbxylic acidwith diazo compounds. of ortho-aminohydro'xy bodies of' the aromaticseries Or of halogen-, nitroor sulfo derivatives thereof. Thus,dyestufls are obtained oi a pronounced mordant character, giving on'wool, when treated in a chrome bath, olive-green to greenish-blackdyeings of excellent properties as to fastness. The new dyestufl's are bfar superior to the products hlt-herto used br the said purpose,particularly as regards their. fastness to washing, fulling and potting.Besides, the

dyebaths prepared with them are exhausted to a much greater extent]Moreover the new dyestufi's have the valuable property of giving dyeingsby the one-bath chroming process.

The dyestuffs can be produced by coupling the diazo compound of anortho-aminohydroxy body of thearomatic series Obtained in the usualmanner, with an alkaline solu-' tion of2.6-dihydroxynaphthalene-3-carboxy lic acid and isolating the dyestuffsby salting out or in another similar manner.

v The following-examples serve to illustrate our invention, but they arenot intended to limit it thereto; the parts are by weight:

(1.) 189 parts of Q-amino-lj-phenolA-sulfonic'acid are dissolved inwater, mixed with 360 parts of hydrochloric acid of 20 B. and

diazotized by means of a. solution of 7 0 parts of sodium nitrite. Thediazo solution thus prepared is coupled with a solution of 204 parts of'2.6-dihydroxynaphthalene-3-carboxylic acid in the presence of 500 partsof calcined sodium carbonate, and when the cou' pling is complete, thedyestufl which partly separates as a dark powder, is completely isolatedby adding common salt. It dyes wool in the single-bath chroming processolivegreen tints of excellent properties as to fastness.

The dyestufl' has the following composi-" 03B OH 0H is isolated in theusual manner dyes wool in y the chrome bath olive-green lent fastnessproperties.

t ,'Th e dyestufi has the following ion:

tints of excelcomposi- I OH I 1 oon 2H 154 parts of4-nitro-2-aminophenol are dlssolved 1n water, mixed with 360 parts ofhydrochloric acid of 20 B. and diazotized with a solution of parts ofsodium nitrite.

The diazo compound 1s then run into a solu tion of 204: parts of2'.6-dihydroxynaphtha- I lene-3-carboxylic acid, to which 500 parts ofcalcined-sodium carbonate have been added.

The dyestufi, which separates as a dark powder, is isolated as usual. Itdyes wool bythe single-bath chroming process olive-green shades ofexcellent fastness to washing, fulling and potting. I

soaH

' with a solution of 204 parts of 2.6-dihyd'roxy- The dyestufi has thefollowing compositionz (4.) 234 parts of 2-amino-1-enol-4-nitro-fi-slilfomc acid are mixed wi; water and 360 parts ofhydrochloric acid of 20 B; and diazotized in the usual manner by meansof a solution of 70 parts of sodium mtrite. The diazo compound thus 7prepared is coupled naphthalene-fi-carboxylic acid in the presence of500 parts of calcined sodium carbonate, dyestufi isolated byaddingcommon t. It dyes wool both in' and the separa I the-chroming proc'esandin the one-bath diazo compoun and the resulting It dyes wool both in thechroming process P7 8 1 chroming process dark 'green tints of excel-slent pro rties as to fastness.

The yestufi has the following tion:

on on 80111 NfNf 1 (5.) of. 2 amino-4-chloro-6- nitro-l-phenol are mixedwith water and 360' parts of" hydrochloric acid ofv20 B. and diazotizedmthe usualmannerlby means of a solution of 70 arts of nitrite. The

thus obtained is coupled with a solution of 204 parts of2.6-dihydroxynaphthalene-awarbtixylic acid in the presence of 7500 partsof calcined sodium carbonate, dyedufi is isolated as usual.

and m the one-bath chroming ish-blaek shades of excellent astnessproptionz rl I 'd d 1. ep'roce'ss-o preparing mor ant" yestufis bycombining the \diazocomaoun'd of an ortho-amino'hy roxy comgpoun of thearomatic series with 2.6-dihy I lene-3-carboxylig acid.

stuff by combining the diazo compound 0 12- 3. Asnew pr stantiall'yidenticzil with the dyestufis pro-j duced .liythe hereindescribedprocesso'f com- ;aminohydroxy compound of the aromatic series with-2.6-dih droxynaphtha1ene-3-carxylic acid, said yestufis being darkpowamino-lhenol-4-n'itro-6-sulfonic acid with 2.6-dihy. roxynahthalene-3 carbogrylicacid;-

ucts, mor'dant dyest'ufis subthe diazo compound of an ortho- 2. Theprocess'of preparing'amoi-dant d ev .ders dyeing wool 1n thechrome-batholive-'3' green to greenish-black of excellent propertiesastofastnessg-f 4. As anew themordant'dyes'tufi duced bi the hereindwcribed processof com}- bining t nol-4-nitro 6-sulfonic acid .with "2.hydroxynaphthalene-fl-carboxylic acid, the 831d dyestufi being a d 1:powder; dye' ,wool both in the chromin process andvin e one-. bath.chroming p 5. Matenals dyed with the dyestufis referred to-in claim 3.-6. Mater'ials dyed with ferre'dtoinclaim.

In- 7 ony whereoi we aflix-our signatures.- ALFBED'PBILIPS.

the dyestufi e dim compound of 2-ami'no-1- 'hel I I evcQ of ex- '1 Icellent properties as. to fashim substantiallyi entical withthedyestufiprm

